Structure of (-)-neodysidenin from Dysidea herbacea. Implications for biosynthesis of 5,5,5-trichloroleucine peptides.

Abstract

[structure: see text]Neodysidenin was isolated from the marine sponge Dysidea herbacea (Keller 1889) collected on the Great Barrier Reef. The complete configuration was obtained from a combination of methods, including capillary electrophoresis of Marfey's derivatives. Neodysidenin belongs to the L-series of trichloroleucine peptides, and the configuration of the N-methyl thiazolyl alanine residue (13R) is opposite to that of dysidenin.